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Jamaica via Montego Bay

Jamaica continues to impress as a world-famous destination for travelers looking to enjoy beautiful beaches, ocean adventures, and romantic vacation packages.
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Now accepting reservations through April 13, 2020. ​​​​

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Earn 1,500 more Rapid Rewards® points per Member on vacations to Jamaica.



Book a flight + hotel package to Jamaica and earn 1,500 more Rapid Rewards points per Member.*

Book: 10/1/19 – 10/28/19 by 6:00 p.m. CT
Travel: 10/2/19 – 3/5/20
One-day advance purchase is required.
Restrictions and exclusions may apply.

Enjoy a wide variety of hotels and resorts throughout Jamaica including all-inclusive resorts in Montego Bay, Negril, and Ocho Rios. Jamaica is an island paradise with resorts lining the picturesque shoreline. There are plenty of choices when it comes to Jamaica resorts and hotels to fit both your style and your budget. Plan for a worry-free experience with an all-inclusive resort where the room, restaurants, drinks, and entertainment are all included in your Southwest Vacations® package price. Jamaica is a great choice for your next beach vacation.​​

Here are a few of our most popular Jamaica via Montego Bay resorts:

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Jamaica via Montego Bay deals from Milwaukee (MKE)

Score great deals on all-inclusive beach vacation packages to Jamaica where you can have a picture-perfect tropical getaway. Southwest Vacations makes it easy to plan the best vacation for your budget, offering weekly deals on travel and resorts. Check out our deals page for more exciting offers.


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    Featured things to do.

    Southwest Vacations has activities, tours, and attractions to add to your vacation. View all of your options in the Things to Do section during the booking process.


    Here are a few ways to spend your time:

    • Soak in the crystal clear waters of Doctor’s Cave Beach and Seven Mile Beach.
    • Enjoy fresh seafood, local Jamaican jerk cuisine, and premium dining options.
    • Capture the spirited nightlife on Montego Bay’s Hip Strip.
    • Raft down the Ocho Rios at Dunn’s River Falls.
    • Take a catamaran snorkeling cruise.
    No matter what you plan to do, Southwest Vacations can help you book your ideal Jamaica all-inclusive vacation package. Book a Jamaica resort today and learn about the benefits of choosing an all-inclusive vacation package.​

    Additional information on Jamaica via Montego Bay activities:

    Discover everything that beautiful Jamaica has to offer. The island nation is rich in culture, natural beauty, and exudes all-around fun energy. Whether you are bringing the kids and looking for a family vacation package, or if you are hoping to explore the history and people of Jamaica with a cultural vacation package, Southwest Vacations has you covered. Jamaica’s many all-inclusive resorts offer amenities appealing to everyone from families to couples, while those looking to soak up the local culture can visit local markets, try amazing island cuisine, and dance to lively local reggae music.

    Activities and attractions abound throughout Jamaica. The most popular activity is of course enjoying the beach with its crystal clear water and white sandy beaches—this is why so many people love a Jamaica vacation! Beach activities in Jamaica range from relaxing while sunbathing and taking a dip in the warm water to more action-packed activities like snorkeling, diving, and taking a catamaran cruise at sunset. Adventure seekers can hike to waterfalls, ride ATVs, and soar through the air on a zip line.

    There is so much to do in Jamaica and so many places to explore. Montego Bay is a hub for nightlife and entertainment. Ocho Rios is famous for great dive sites and Dunn’s River Falls, a national treasure and one of Jamaica’s most famous landmarks. Negril’s Seven Mile Beach not only offers a long coastline of beaches to enjoy by day, but many fun restaurants, bars, and dance clubs to enjoy at night too. When it comes to things to do in Jamaica, your options are endless.

    Flight service to Montego Bay may vary based on departure, date, and origin city. View our flight information, so you can vacation with ease.

    *One-day advance purchase is required. 1,500 Rapid Rewards points will be awarded to each Member on flight + hotel vacation packages of five nights or longer to Montego Bay, Jamaica (MBJ). To earn Rapid Rewards points for a vacation package, enter each Passenger's Rapid Rewards account number during checkout. Rapid Rewards account numbers can also be entered by visiting your account at Southwest.com​, when you check in online for your flight, or by providing your account number at the airport counter or gate before boarding your flight. Please allow up to eight weeks after completed qualifying travel for the 1,500 Rapid Rewards points to be posted to each Member on the reservation with a Rapid Rewards account number at time of booking. Rapid Rewards points are awarded in addition to the base Rapid Rewards points for air offered with any package purchase and indicated during the booking process and on travel documents. Points do not count towards A-List or A-List Preferred status. Points will be rewarded if booked 10/1/19 – 10/28/19 by 6:00 p.m. CT for travel 10/2/19 – 3/5/20. All Rapid Rewards rules and regulations apply and can be found at Southwest.com/rrterms.​

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